True Linux Confessions: Leaving Gmail for Outlook.com

screeshot of Outlook

I sometimes feel a little bit over-invested in the Google ecosystem. Google is a double-edged sword, because the more invested I am in their products, the easier so many things are, but the downside is that I’m at their mercy whenever they decide to make changes, UI or otherwise. Plus, the more Google products I use, the more information they have about me, which doesn’t always feel ideal from a privacy perspective (although The New York Times is surprisingly OK with the idea). With that in mind, a few months ago I decided to get myself off of Gmail. To my surprise, I wound up switching to Outlook.com.

I’d heard a lot of surprisingly positive things about Outlook.com. Plus, when I was writing my book, I was surprised (shocked, even) how well so many Microsoft services compared to the Google versions (Microsoft does lose points for naming products, though). As you might guess, I’ve never been a huge Microsoft fan. I’ve always resented their monopoly and for a long time, they released subpar products because of that monopoly. For a long time, Microsoft didn’t innovate because they didn’t need to. But with Google and Apple coming at Microsoft all the time on all kinds of fronts, I no longer see Microsoft as a dominant force. Instead, I see it as more a broken boxer trying to make one final run at a belt. Where Hotmail always felt like Microsoft had been sentenced to run it, Outlook.com is much more cohesive and thoughtful. It allows you to send through a domain for free, via their domains tool. The web interface is great, with a true desktop client feel. For instance, pressing the delete key actually deletes a message. The spam filtering is also great. I’ve been reviewing the spam folder each day, and misfires are extremely rare. Plus, like most spam filters, it learns as you mark things as spam and not spam.

As I mentioned above, I have Outlook.com configured for my domain, but it also allows me to send messages through other accounts. It also has a great aliasing concept, where I can create Outlook accounts and associate them with my master account. It’s not something I use, but it’s a smart way to handle multiple identities.

The IMAP implementation is also fantastic, in that it’s standard. Google’s IMAP always felt like it played by its own rules, what with the weird way it displayed labels and the fact that delete didn’t really delete but Outlook.com runs flawlessly through Thunderbird and K9 (my phone email client, although the Outlook.com Android app also works well). I’m not making due with Outlook.com — I actively prefer it to Gmail. Where Gmail often made me feel like I was working the way the Gmail team wanted me to, Outlook.com provides the flexibility to work the way I want to. Just about every time I’ve thought “I wish Outlook.com let me do X,” I’ve gone into the settings and found a way to make it happen.

Now to be clear, I am in no way Google-free. I still use Google Calendar because my wife and I share events (and because I fear my calendar is too big and complicated to export). I still use Google Hangouts to chat with people, although now that I’m not using Gmail, I’m using the Hangouts Chrome extension (Outlook.com also supports Hangouts). I also didn’t bother to move my old Gmail over to Outlook, because it seemed unnecessary. I rarely need to go back through my email and if I do, I know where the Gmail messages are. However, Google recently made moving mail fairly simple.

Before settling on Outlook.com, I spent a fair amount of time researching services (I knew I didn’t want to be responsible for my own server) on EmailDiscussions and decided to start my exploration with Fastmail, which is very highly-rated and recommended pretty much everywhere.

Fastmail is robust, with great support for multiple accounts. They’re also considered very strong from a privacy perspective, but the spam filtering was just prohibitively bad. I have a few accounts that have been public for a decade or more, so I get hit with spam pretty hard. I also wasn’t able to get two-step authentication working. In general, the documentation wasn’t great and after a couple of weeks, I decided to explore other options.

My next stop was hosted Exchange. Exchange is an industry standard and the price was ridiculously low ($4/month). I got Exchange up and running but it was way, way, way more than I needed in some ways (especially for a single user), and not enough in others (like it didn’t offer a convenient way to handle multiple email accounts).

In terms of leaving Google, this is, admittedly, not a huge victory. But it did help me to diversify a bit. To a certain extent, Android users need to be invested in Google or your phones become useless. That’s the price of convenience and I’m OK with it. But moving off of Gmail, even if the move is to a Microsoft product, feels good. Outlook.com is solid, with a nice interface, and great IMAP support. I’m shocked that given a choice between a Google product and a Microsoft one, the Microsoft one is ultimately the one that provides more freedom in how I use it. If you’re no longer interested in Gmail and you’re OK with US-hosted servers, and all that that implies, Outlook.com is a great option — even for Linux users.

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